Let’s say your players are travelling through the wilderness and occasionally come upon a fort, or are travelling through a settled land and come across villages pretty regularly. You could draw up a ton of villages but here’s an easier way.
Decide on a number of d6s to roll. This relates to population.
Roll your d6s all at once so they scatter a little. Each pip is a family. Each die is a number of families living close together. Where the dice fall is where these buildings are in relation to each other.
Results of 1 are shops or inns. The first shop in any village is definitely going to be a general store, but any additional shops could be specialists who attract business from the surrounding villages or else travel regularly. Or it could be a church. Maybe the church can act as a combination inn and general store, since you could ask to sleep on the floor and they might have some used gear from failed adventurers they would cough up for a small donation.
Results of 2-5 are farming families. Their hovels are grouped together and walled in so the chickens and pigs don’t get out.
Results of 6 are wealthy people, such as minor nobility or merchants or landowners. The first family is their own, another is a group of servants, and the remaining are attached peasants.
If you don’t get any 6s, then the highest dice are the local gentry. If there is only 1 of the highest dice, there’s just one, but if there are multiples then you have multiple wealthy people.
Example: 1, 4, 4, 5, 5
One general store, two sets of 4 peasant families, one local noble + servants + 3 serf families, one merchant + servants + 3 employee families.
Example: 2, 2, 2, 3
Three pairs of peasants, one headman with his family + servants + scattered men-at-arms.
Example: 5, 6, 6, 6
A stockade of five peasant families, and three local wizards’ towers each walled in with servants and serf families.
One family should be considered as 6 people, or you could roll d6 adults + d6 children or something. I’d say the content of the family is another layer down which you might care about enough to write a method for generating them.
Now you’ve got the layout and content of the village. Draw blocks on the paper to reflect area of control – that is, the plot of land around the buildings – and then draw in the buildings wherever the dice actually fell. Draw roads along the borders between the plots. If it seems like everyone has a long driveway, consider adding a village green in the middle to soak up some extra space with a road surrounding it. Or scoot the dice a little closer together to make it look more village-y.
You could determine what a given building is by making a list of 1-4 and looking at which side of the die was facing you (for this you need to use dice with numbers instead of pips). 1 = top, 2 = right side, 3 = bottom, 4 = left side. For example, you could roll a 3 (peasant families) and if the right side of the number 3 is toward you that peasant family does shepherding. In general, I’d rather just blast through those decisions with stuff that makes more sense, otherwise you could end up with six villages in a row that each have a blacksmith but no other stores …
(Props to Zak for turning me on to die-drop generation which, among other Vornheim and blogstuff, helped inspire this)